Which CEOs are actually worth keeping around?

That's a feature of Market Socialism, but we can't call it that because sOcIalIsM sCaRy, so let's go with Democracy in the Workplace.

Socialism is of course democratic. When people say "socialism is bad" what they mean is Socialism is good, and they're thinking about Communism, which is actually also good but has never really been implemented properly.
- Communism could not be implemented properly, without first moving through socialism, that is, worker control and collective ownership of their productive workplace, but all over the world. A radical social transformation, international in scope, in which we can begin to assess human need and begin to distribute based on it, democratic from top to bottom.
  
  But the ruling class won't just give over control it has to be taken, with collective power.
I mean, that's literally the conclusion that Richard Wolff came to. Call it whatever, just as long as we do it.

Pirates had some of the purest forms of democracy. Their captains were democratically elected in many cases as well. Not sure why they came to mind when you said this... But if your going to rip people off, and democratically pick your leader, pirates formed your company right

Seems like the pirate environment is especially suited to this type of democracy. Pirate ships operate outside the protections afforded by law, so the only thing really preventing pirate captains from being ousted (or murdered) is the crew's support.

I guess a CEO would need to maintain shareholder support, but shareholders are generally fairly disconnected from the company's day to day operations. Most individuals own shares through mutual funds or ETFs, which means they don't actually have share ownership themselves and can't vote. All you have is the fund owing you a fiduciary duty to vote in your best interests, which generally translates to whatever makes the most money. So the CEO just needs to keep a few large institutions happy, and possibly some large wealthy individual shareholders that he knows from the rotary club (where the heads of aforementioned institutions are also members)

In other words, the way the financial system is set up systematically deprives the less wealthy from their right to have a say in the operation of the companies they nominally own a part of.

At the start of the Russian Revolution, the Soviets tried that. Even they quickly discovered that pure democracy didn't work well when choosing "the boss." They even went so far as to remove ranks from the military. Which failed even faster.

Turns out, "the boss" often can't afford to be popular or buddies with everyone when making decisions.

Che Guevara wrote about in his book Critical Notes on Political Economy about how workers who are given full autonomy in their enterprises actually can become antagonistic towards society because they benefit solely from their own enterprise succeeding at the expense of all others, and thus they acquire similar motivations to the capitalist class, i.e. they want deregulations, dismantling of the public sector, more power to their individual enterprise, etc.

The solution is not to abandon workplace democracy but to balance it out also with public democracy. You have enterprises with a board that is both a mixture of direct appointments from the workers at that company with their direct input, as well as appointments by the public sector / central government. The public appointments are necessary to make sure the company is keeping inline with the will of everybody and not merely the people at that specific enterprise, because the actions of that enterprise can and does affect the rest of society.

Workplaces need to be democratic, but also not autonomous from the democratic will of the rest of society.
- "on a long enough timeline, the primary purpose of every organization becomes its own continued existence"

Yeah... no.

Reality is sometimes the boss has to be bossy. Quadrupling salaries and cutting 4 days a week from the schedule sounds great for employees until the business fails.

What should be implemented is a maximum ratio of executive/worker pay (including contractors so they don't just outsource cheap labor to cheat the system) based on 5-year averages.

Without the 5-year rule, and new CEO can come in, give everyone massive raises, and burn the company down for a quick buck.

The boss can still be bossy if elected. Your 5 year rule is silly and does not address the overlying problem, which is that the CEO works for the shareholders and they only care about making record quarterly profit gains at any cost.
The boss does sometimes have to be bossy. If the workers have a stake in the company that actually matters, then they also actually care about the outcome that the company faces.

You're not going to vote to drive something into the ground if you think it will provide you with more value not dismantled and in your pocket.

Workers aren't idiots any more than CEOs are. It's why worker owned co-ops that elect their management do sometimes vote to reduce their own wages. They have a fair stake and want what's best for the business because it's best for them.
- What if they work for a company where the vast majority of positions aren't viewed as a "career" jobs?
  
  Not many people want to flip burgers or stock shelves the rest of their lives. If 80% of the workplace doesn't plan on sticking with the company anyway, why wouldn't they elect the person who will triple their salary for a few months before they jump ship to another burger chain?
  
  With that bump in payment, they can afford to spend a few months looking for a job after the one they have goes away because the business went under.

You could in fact create a company that operates like that if you wanted. The problem is that you can't force every company to organize according to your preferences.

You could if you worked together... And your preferences were the majority's preferences
- You can force a lot of things if you have the majority. Doesn't mean you should.
If Congress writes the law then it can be so.
Except if it's capitalism right, because this bullshit is happening now